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A racemic as well as an EPC-synthesis of the cis-hydrindene subunit of the cochleamycins, physiologically active microbial secondary metabolites, are reported. The five stereogenic centres of this subunit are introduced in high stereoselectivity in a short sequence by intermolecular Diels–Alder reaction, stereoselective methylation and hydride reduction. Cyclisation via nucleophilic addition, acidic...
The EPC-synthesis of the cis-hydrindene subunit of the macquarimicins, antibiotics with antitumour and anti-inflammatory activity, has been achieved. Desymmetrization of cis-1,4-cyclopent-2-enediol was succeeded by Diels–Alder reaction and functional group transformations to a tricyclic ketone. Regio- and stereoselective methylation via Claisen condensation and hydrogenation was followed by nucleophilic,...
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